# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jcv1701
_database_code_depnum_ccdc_archive 'CCDC 1588578'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_STRVA01_jcv1701             
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: The low anomalous scattering power of the atoms in this structure 
(none heavier than oxygen) implies that the data cannot be used for absolute 
structure assignment, thus the Flack parameter is meaningless.  Absolute 
structure was assigned on the basis of the known stereochemistry of the 
starting material and the synthetic methodology.
;
_vrf_PLAT907_jcv1701             
;
PROBLEM: Flack x > 0.5, Structure Needs to be Inverted? .       1.00 Check 
RESPONSE: The low anomalous scattering power of the atoms in this structure 
(none heavier than oxygen) implies that the data cannot be used for absolute 
structure assignment, thus the Flack parameter is meaningless.  Absolute 
structure was assigned on the basis of the known stereochemistry of the 
starting material and the synthetic methodology.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(1S)-1-phenylethyl (2R)-2-{[(carbamoylamino)oxy]methyl}oxirane-2-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 N2 O5'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9509(12)
_cell_length_b                   7.1789(12)
_cell_length_c                   16.121(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.821(18)
_cell_angle_gamma                90
_cell_volume                     688.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3325
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      69.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.884
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5229
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3111
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.751
_diffrn_reflns_theta_max         67.657
_diffrn_reflns_theta_full        67.657
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.834
_reflns_number_total             2076
_reflns_number_gt                1582
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_max     0.655
_reflns_Friedel_fraction_full    0.655

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1451P)²+0.5435P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 372 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.0(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2076
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2560
_refine_ls_wR_factor_gt          0.2308
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1885(9) -0.3259(8) 0.2379(4) 0.0484(15) Uani 1 1 d . . . . .
O2 O 0.1420(11) 0.1344(9) 0.3203(4) 0.0575(18) Uani 1 1 d . . . . .
O3 O 0.2967(10) 0.0322(7) 0.2020(4) 0.0483(15) Uani 1 1 d . . . . .
O4 O -0.1522(9) -0.1901(8) 0.3665(4) 0.0438(14) Uani 1 1 d . . . . .
O5 O -0.5045(9) -0.0176(8) 0.5189(4) 0.0433(14) Uani 1 1 d . . . . .
N1 N -0.2619(12) -0.1849(10) 0.4439(5) 0.0490(19) Uani 1 1 d . . . . .
H1N H -0.2653 -0.2818 0.4772 0.059 Uiso 1 1 calc R U . . .
N2 N -0.2906(12) 0.1322(9) 0.4247(5) 0.0470(18) Uani 1 1 d . . . . .
H2NA H -0.3441 0.2424 0.4378 0.056 Uiso 1 1 calc R U . . .
H2NB H -0.1891 0.1221 0.3858 0.056 Uiso 1 1 calc R U . . .
C1 C 0.3950(12) -0.3082(11) 0.2821(5) 0.0419(19) Uani 1 1 d . . . . .
H1A H 0.5222 -0.2488 0.2533 0.050 Uiso 1 1 calc R U . . .
H1B H 0.4375 -0.4088 0.3212 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2019(11) -0.1909(11) 0.3029(5) 0.0377(17) Uani 1 1 d . . . . .
C3 C 0.2103(11) 0.0113(10) 0.2763(5) 0.0372(17) Uani 1 1 d . . . . .
C4 C 0.0799(13) -0.2293(11) 0.3817(6) 0.0448(19) Uani 1 1 d . . . . .
H4A H 0.0997 -0.3612 0.3981 0.054 Uiso 1 1 calc R U . . .
H4B H 0.1392 -0.1493 0.4269 0.054 Uiso 1 1 calc R U . . .
C5 C -0.3628(11) -0.0186(12) 0.4636(6) 0.0416(18) Uani 1 1 d . . . . .
C6 C 0.3517(14) 0.2248(11) 0.1765(6) 0.0420(19) Uani 1 1 d . . . . .
H6 H 0.2497 0.3134 0.2055 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5908(15) 0.2615(14) 0.2044(7) 0.055(2) Uani 1 1 d . . . . .
H7A H 0.6358 0.3866 0.1868 0.066 Uiso 1 1 calc R U . . .
H7B H 0.6905 0.1690 0.1795 0.066 Uiso 1 1 calc R U . . .
H7C H 0.6015 0.2528 0.2650 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3062(11) 0.2361(10) 0.0846(5) 0.0364(18) Uani 1 1 d . . . . .
C9 C 0.1039(12) 0.3119(11) 0.0546(6) 0.0442(19) Uani 1 1 d . . . . .
H9 H -0.0034 0.3563 0.0930 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0568(13) 0.3237(12) -0.0291(6) 0.050(2) Uani 1 1 d . . . . .
H10 H -0.0817 0.3754 -0.0480 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2104(14) 0.2606(12) -0.0849(6) 0.049(2) Uani 1 1 d . . . . .
H11 H 0.1770 0.2665 -0.1427 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4121(14) 0.1890(11) -0.0580(6) 0.0438(19) Uani 1 1 d . . . . .
H12 H 0.5187 0.1479 -0.0973 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4622(11) 0.1757(10) 0.0269(5) 0.0391(18) Uani 1 1 d . . . . .
H13 H 0.6023 0.1257 0.0451 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.417(10) . ?
O1 C2 1.429(10) . ?
O2 C3 1.207(10) . ?
O3 C3 1.318(10) . ?
O3 C6 1.481(9) . ?
O4 N1 1.416(9) . ?
O4 C4 1.427(10) . ?
O5 C5 1.236(9) . ?
N1 C5 1.375(11) . ?
N2 C5 1.326(11) . ?
C1 C2 1.467(10) . ?
C2 C4 1.497(11) . ?
C2 C3 1.515(11) . ?
C6 C8 1.504(12) . ?
C6 C7 1.510(12) . ?
C8 C13 1.393(10) . ?
C8 C9 1.401(11) . ?
C9 C10 1.376(13) . ?
C10 C11 1.370(13) . ?
C11 C12 1.370(12) . ?
C12 C13 1.400(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 62.1(5) . . ?
C3 O3 C6 116.7(6) . . ?
N1 O4 C4 108.2(6) . . ?
C5 N1 O4 115.8(7) . . ?
O1 C1 C2 59.4(5) . . ?
O1 C2 C1 58.6(5) . . ?
O1 C2 C4 118.3(7) . . ?
C1 C2 C4 118.6(7) . . ?
O1 C2 C3 116.4(7) . . ?
C1 C2 C3 117.1(6) . . ?
C4 C2 C3 115.8(7) . . ?
O2 C3 O3 126.1(7) . . ?
O2 C3 C2 121.5(7) . . ?
O3 C3 C2 112.4(7) . . ?
O4 C4 C2 107.4(7) . . ?
O5 C5 N2 124.4(8) . . ?
O5 C5 N1 118.4(8) . . ?
N2 C5 N1 117.0(7) . . ?
O3 C6 C8 106.7(6) . . ?
O3 C6 C7 106.9(7) . . ?
C8 C6 C7 116.1(7) . . ?
C13 C8 C9 118.0(8) . . ?
C13 C8 C6 121.9(7) . . ?
C9 C8 C6 120.1(7) . . ?
C10 C9 C8 121.6(8) . . ?
C11 C10 C9 119.7(8) . . ?
C10 C11 C12 120.4(9) . . ?
C11 C12 C13 120.6(8) . . ?
C8 C13 C12 119.8(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O4 N1 C5 119.5(7) . . . . ?
C1 O1 C2 C4 -108.0(8) . . . . ?
C1 O1 C2 C3 107.1(7) . . . . ?
O1 C1 C2 C4 107.4(8) . . . . ?
O1 C1 C2 C3 -105.8(8) . . . . ?
C6 O3 C3 O2 11.4(12) . . . . ?
C6 O3 C3 C2 -169.0(7) . . . . ?
O1 C2 C3 O2 152.8(7) . . . . ?
C1 C2 C3 O2 -140.8(8) . . . . ?
C4 C2 C3 O2 7.0(11) . . . . ?
O1 C2 C3 O3 -26.8(9) . . . . ?
C1 C2 C3 O3 39.7(10) . . . . ?
C4 C2 C3 O3 -172.6(7) . . . . ?
N1 O4 C4 C2 -167.1(6) . . . . ?
O1 C2 C4 O4 -77.8(8) . . . . ?
C1 C2 C4 O4 -145.5(7) . . . . ?
C3 C2 C4 O4 67.3(8) . . . . ?
O4 N1 C5 O5 162.7(7) . . . . ?
O4 N1 C5 N2 -21.1(11) . . . . ?
C3 O3 C6 C8 -145.4(6) . . . . ?
C3 O3 C6 C7 89.8(8) . . . . ?
O3 C6 C8 C13 -82.6(8) . . . . ?
C7 C6 C8 C13 36.4(11) . . . . ?
O3 C6 C8 C9 98.5(8) . . . . ?
C7 C6 C8 C9 -142.5(8) . . . . ?
C13 C8 C9 C10 1.3(11) . . . . ?
C6 C8 C9 C10 -179.8(7) . . . . ?
C8 C9 C10 C11 -0.1(12) . . . . ?
C9 C10 C11 C12 -1.2(12) . . . . ?
C10 C11 C12 C13 1.3(12) . . . . ?
C9 C8 C13 C12 -1.2(10) . . . . ?
C6 C8 C13 C12 180.0(7) . . . . ?
C11 C12 C13 C8 -0.1(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O5 0.88 2.18 2.832(9) 130.7 2_446
N2 H2NA O5 0.88 2.07 2.944(9) 172.0 2_456
N2 H2NB O2 0.88 2.25 3.096(9) 161.0 .

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.098


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene/EtOAc (3:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jcv1705
_database_code_depnum_ccdc_archive 'CCDC 1588579'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(1R)-1-phenylethyl (2S)-2-{[(carbamoylamino)oxy]methyl}oxirane-2-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.92380(10)
_cell_length_b                   7.17870(10)
_cell_length_c                   16.1585(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8223(8)
_cell_angle_gamma                90
_cell_volume                     687.07(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      73.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7597
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4927
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.735
_diffrn_reflns_theta_max         73.950
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2754
_reflns_number_gt                2674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.979

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0037(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2754
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3141(2) 0.8250(2) 0.26192(8) 0.0351(3) Uani 1 1 d . . . . .
O2 O 0.3513(3) 0.3626(2) 0.17921(8) 0.0424(4) Uani 1 1 d . . . . .
O3 O 0.2068(2) 0.46650(18) 0.29919(8) 0.0349(3) Uani 1 1 d . . . . .
O4 O 0.6520(2) 0.68546(19) 0.13333(7) 0.0313(3) Uani 1 1 d . . . . .
O5 O 1.0047(2) 0.51275(19) -0.01896(8) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.7617(3) 0.6803(2) 0.05578(10) 0.0362(4) Uani 1 1 d . . . . .
H1N H 0.846(4) 0.787(4) 0.0449(16) 0.041(6) Uiso 1 1 d . . . . .
N2 N 0.7902(3) 0.3625(2) 0.07595(10) 0.0335(3) Uani 1 1 d . . . . .
H2NA H 0.681(5) 0.372(4) 0.1073(16) 0.046(7) Uiso 1 1 d . . . . .
H2NB H 0.856(5) 0.257(5) 0.0607(18) 0.053(8) Uiso 1 1 d . . . . .
C1 C 0.1033(3) 0.8089(3) 0.21824(11) 0.0364(4) Uani 1 1 d . . . . .
H1A H 0.0612 0.9094 0.1790 0.044 Uiso 1 1 calc R U . . .
H1B H -0.0248 0.7514 0.2475 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2958(3) 0.6887(3) 0.19721(9) 0.0284(4) Uani 1 1 d . . . . .
C3 C 0.2906(3) 0.4870(3) 0.22380(10) 0.0290(4) Uani 1 1 d . . . . .
C4 C 0.4188(3) 0.7291(3) 0.11879(11) 0.0328(4) Uani 1 1 d . . . . .
H4A H 0.3571 0.6522 0.0729 0.039 Uiso 1 1 calc R U . . .
H4B H 0.4018 0.8621 0.1037 0.039 Uiso 1 1 calc R U . . .
C5 C 0.8607(3) 0.5141(3) 0.03668(10) 0.0286(3) Uani 1 1 d . . . . .
C6 C 0.1499(3) 0.2736(3) 0.32456(11) 0.0330(4) Uani 1 1 d . . . . .
H6 H 0.2514 0.1843 0.2956 0.040 Uiso 1 1 calc R U . . .
C7 C -0.0908(4) 0.2391(3) 0.29683(12) 0.0424(5) Uani 1 1 d . . . . .
H7A H -0.1355 0.1126 0.3124 0.051 Uiso 1 1 calc R U . . .
H7B H -0.1904 0.3293 0.3234 0.051 Uiso 1 1 calc R U . . .
H7C H -0.1029 0.2529 0.2366 0.051 Uiso 1 1 calc R U . . .
C8 C 0.1946(3) 0.2618(2) 0.41664(11) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.3976(3) 0.1862(3) 0.44551(13) 0.0362(4) Uani 1 1 d . . . . .
H9 H 0.5037 0.1398 0.4071 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4466(3) 0.1777(3) 0.52942(14) 0.0404(4) Uani 1 1 d . . . . .
H10 H 0.5871 0.1285 0.5482 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2906(4) 0.2411(3) 0.58607(12) 0.0376(4) Uani 1 1 d . . . . .
H11 H 0.3238 0.2357 0.6437 0.045 Uiso 1 1 calc R U . . .
C12 C 0.0861(3) 0.3121(3) 0.55814(11) 0.0338(4) Uani 1 1 d . . . . .
H12 H -0.0224 0.3530 0.5968 0.041 Uiso 1 1 calc R U . . .
C13 C 0.0386(3) 0.3239(2) 0.47390(11) 0.0293(4) Uani 1 1 d . . . . .
H13 H -0.1012 0.3747 0.4553 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.430(2) . ?
O1 C2 1.435(2) . ?
O2 C3 1.206(2) . ?
O3 C3 1.330(2) . ?
O3 C6 1.484(2) . ?
O4 N1 1.4205(17) . ?
O4 C4 1.432(2) . ?
O5 C5 1.248(2) . ?
N1 C5 1.367(3) . ?
N2 C5 1.330(2) . ?
C1 C2 1.474(2) . ?
C2 C4 1.499(2) . ?
C2 C3 1.511(3) . ?
C6 C7 1.509(3) . ?
C6 C8 1.510(2) . ?
C8 C13 1.391(2) . ?
C8 C9 1.393(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.389(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 61.92(11) . . ?
C3 O3 C6 116.45(13) . . ?
N1 O4 C4 108.27(13) . . ?
C5 N1 O4 115.18(15) . . ?
O1 C1 C2 59.19(11) . . ?
O1 C2 C1 58.89(12) . . ?
O1 C2 C4 116.83(16) . . ?
C1 C2 C4 117.95(16) . . ?
O1 C2 C3 116.61(13) . . ?
C1 C2 C3 118.45(15) . . ?
C4 C2 C3 115.99(15) . . ?
O2 C3 O3 125.72(17) . . ?
O2 C3 C2 122.17(15) . . ?
O3 C3 C2 112.09(14) . . ?
O4 C4 C2 107.35(14) . . ?
O5 C5 N2 124.06(17) . . ?
O5 C5 N1 117.98(17) . . ?
N2 C5 N1 117.89(15) . . ?
O3 C6 C7 106.78(16) . . ?
O3 C6 C8 106.69(14) . . ?
C7 C6 C8 115.79(15) . . ?
C13 C8 C9 118.73(17) . . ?
C13 C8 C6 121.92(16) . . ?
C9 C8 C6 119.35(16) . . ?
C10 C9 C8 120.86(17) . . ?
C9 C10 C11 120.00(18) . . ?
C12 C11 C10 119.60(18) . . ?
C11 C12 C13 120.43(17) . . ?
C12 C13 C8 120.34(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O4 N1 C5 -120.52(17) . . . . ?
C1 O1 C2 C4 107.95(18) . . . . ?
C1 O1 C2 C3 -108.66(17) . . . . ?
O1 C1 C2 C4 -106.06(18) . . . . ?
O1 C1 C2 C3 105.55(17) . . . . ?
C6 O3 C3 O2 -10.4(3) . . . . ?
C6 O3 C3 C2 167.79(15) . . . . ?
O1 C2 C3 O2 -154.31(18) . . . . ?
C1 C2 C3 O2 138.38(19) . . . . ?
C4 C2 C3 O2 -10.6(3) . . . . ?
O1 C2 C3 O3 27.4(2) . . . . ?
C1 C2 C3 O3 -39.9(2) . . . . ?
C4 C2 C3 O3 171.15(15) . . . . ?
N1 O4 C4 C2 166.48(15) . . . . ?
O1 C2 C4 O4 78.67(19) . . . . ?
C1 C2 C4 O4 145.90(16) . . . . ?
C3 C2 C4 O4 -64.9(2) . . . . ?
O4 N1 C5 O5 -162.48(15) . . . . ?
O4 N1 C5 N2 20.5(2) . . . . ?
C3 O3 C6 C7 -88.72(18) . . . . ?
C3 O3 C6 C8 146.90(15) . . . . ?
O3 C6 C8 C13 82.1(2) . . . . ?
C7 C6 C8 C13 -36.5(3) . . . . ?
O3 C6 C8 C9 -98.04(19) . . . . ?
C7 C6 C8 C9 143.31(19) . . . . ?
C13 C8 C9 C10 -1.9(3) . . . . ?
C6 C8 C9 C10 178.29(18) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C6 C8 C13 C12 -179.54(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O5 0.94(3) 1.89(3) 2.826(2) 175(2) 2_755
N2 H2NA O2 0.83(3) 2.29(3) 3.109(2) 170(3) .
N2 H2NB O5 0.89(3) 2.06(3) 2.943(2) 176(3) 2_745

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene/EtOAc (2:1)'
